:Desacetoxyvindoline
{{Chembox
| ImageFile = Desacetoxyvindoline.svg
| ImageSize = 200px
| IUPACName = Methyl 3-hydroxy-16-methoxy-1-methyl-6,7-didehydro-2β,5α,12β,19α-aspidospermidine-3β-carboxylate
| SystematicName = Methyl (3aR,3a1S,5R,5aR,10bR)-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
| OtherNames = Deacetoxyvindoline
|Section1={{Chembox Identifiers
| CASNo = 105119-60-6
| CASNo_Ref = {{Cascite|changed|{{cite web |title=KNApSAcK Metabolite Information - C00051787 |url=http://www.knapsackfamily.com/knapsack_core/information.php?word=C00051787 |website=www.knapsackfamily.com}}}}
| ChEBI = 16957
| KEGG = C02673
| PubChem = 439783
| ChemSpiderID = 388838
| SMILES = CC[C@]12C[C@@]([C@H]3[C@@]4([C@H]1N(CC4)CC=C2)c5ccc(cc5N3C)OC)(C(=O)OC)O
| InChI = 1/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3/t18-,19+,21-,22+,23+/m0/s1
| InChIKey = WNKDGPXNFMMOEJ-RNJSZURPBV
| StdInChI = 1S/C23H30N2O4/c1-5-21-9-6-11-25-12-10-22(18(21)25)16-8-7-15(28-3)13-17(16)24(2)19(22)23(27,14-21)20(26)29-4/h6-9,13,18-19,27H,5,10-12,14H2,1-4H3/t18-,19+,21-,22+,23+/m0/s1
| StdInChIKey = WNKDGPXNFMMOEJ-RNJSZURPSA-N
}}
|Section2={{Chembox Properties
| C=23 | H=30 | N=2 | O=4
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Desacetoxyvindoline is a terpene indole alkaloid produced by the plant Catharanthus roseus. Desacetoxyvindoline is a product formed by the methylation of the nitrogen on the indole ring by the enzyme 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase (NMT).{{cite journal |last1=Liscombe |first1=DK |last2=Usera |first2=AR |last3=O'Connor |first3=SE |title=Homolog of tocopherol C methyltransferases catalyzes N methylation in anticancer alkaloid biosynthesis. |journal=Proceedings of the National Academy of Sciences of the United States of America |date=2 November 2010 |volume=107 |issue=44 |pages=18793–8 |doi=10.1073/pnas.1009003107 |pmid=20956330|pmc=2973921 |bibcode=2010PNAS..10718793L |doi-access=free }} The metabolite is a substrate for desacetoxyvindoline 4-hydroxylase (D4H) which catalyzes a hydroxylation to yield deacetylvindoline.{{cite journal |last1=Vazquez-Flota |first1=Felipe |last2=De Carolis |first2=Emidio |last3=Alarco |first3=Anne-Marie |last4=De Luca |first4=Vincenzo |title=Molecular cloning and characterization of desacetoxyvindoline-4-hydroxylase, a 2-oxoglutarate dependent-dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don |journal=Plant Molecular Biology |date=1997 |volume=34 |issue=6 |pages=935–948 |doi=10.1023/A:1005894001516|pmid=9290645 |s2cid=33942703 }}